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Synfacts 2008(9): 0951-0951
DOI: 10.1055/s-2008-1078643
DOI: 10.1055/s-2008-1078643
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Substituted Tetrahydrofurans by [3+2] Cycloadditions
A. T. Parsons, M. J. Campbell, J. S. Johnson*
University of North Carolina at Chapel Hill, USA
Further Information
Publication History
Publication Date:
22 August 2008 (online)
Significance
The common occurrence of various THF substitution patterns in biologically active compounds makes the advent of new efficient methods to prepare these structures welcome. The authors report a simple procedure to synthesize 2,3,5-trisubstituted tetrahydrofurans from simple starting materials. Vinylcyclopropane (VCP) was prepared in one step from malonate and 1,4-dibromo-2-butene. Low catalyst loadings can be used to obtain 2,5-cis-tetrahydrofurans.